The liquid phase benzopyran composition containing from 70-81% by weight of 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[G]-2-benzopyran having the structure:
(known as “GALAXOLIDE 100”, registered trademark of International Flavors & Fragrances Inc. of New York, N.Y.) and solutions thereof, for example, 50% solutions in diethyl phthalate (known as “GALAXOLIDE 50”, registered trademark of International Flavors & Fragrances Inc. of New York, N.Y.) are among the largest volume aroma chemicals currently in use in commerce. The material is known to impart to consumable materials including fine fragrances and perfumes for use in functional products such as soaps and detergents, a tenacious and substantive musk aroma. As manufactured, the liquid phase benzopyran composition known as “GALAXOLIDE” contains 70-75% by weight of 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[G]-2-benzopyran having the structure:
which structure contains four diastereomeric isomers including the 4R-cis and trans isomers and the 4S-cis and trans isomers. Frater et al. I, U.S. Pat. No. 5,635,471, the specification of which is herein incorporated by reference, discloses that the mixture of the 7R and 7S diastereoisomers have a stronger musk aroma and Frater et al. II, Helvetica Chimica Acta. Vol. 82, 1999, pp. 1656-1665 discloses that the strongest isomer is the (−)-(4S,7R) isomer. GALAXOLIDE as commercially produced and as taught by the art to be produceable, for example, U.S. Pat. No. 3,360,530, the specification for which is herein incorporated by reference, consists of a thick, viscous liquid which can solidify at cold temperatures, for example at 0° C. It is well known to those skilled in the art that this material is difficult to handle either as the highly concentrated viscous liquid or as diluted in a solvent such as diethyl phthalate benzyl benzoate, isopropyl myristate and/or dipropylene glycol. Typically, it is diluted so that the major isomers, indicated by the structure:
make up 50% of the solution, by weight. As currently manufactured, and as disclosed in the prior art, GALAXOLIDE has been reported to have some adverse environmental effects. Accordingly, a need exists to provide a form of GALAXOLIDE that can be used in perfumes, colognes and perfumed articles in substantially lower dosages than heretofore known in the art, thereby protecting the environment.
Solid forms of GALAXOLIDE are disclosed in the prior art, including                (a) Sprecker, U.S. Pat. No. 4,650,603, the disclosure of which is herein incorporated by reference; and        (b) Frater et al. II, U.S. Pat. No. 5,635,471.However, the solid forms of GALAXOLIDE so disclosed in the prior art do not contain the necessary and desirable high percentages, 85-95 weight % of the isomers having the structure:        
which high percentages cause the solid phase benzopyran compositions of our invention to have unobvious, unexpected and advantages organoleptic properties regarding aroma quality, strength and substantivity.